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2-Methylvaleric acid → N-{3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N'-(2-methylpentanoyl)thiourea

HRID 721952
ノート
印刷プレビュー

反応式

HRID 721952 の反応式
S(Cl)(Cl)=O.CC(CCC)C(O)=O.CC(CCC)C(Cl)=O.[CH3:21][CH:22]([CH2:28][CH2:29][CH3:30])[C:23]([N:25]=[C:26]=[S:27])=[O:24].[Cl:31][C:32]1[CH:33]=[C:34]([CH:36]=[CH:37][C:38]=1[O:39][C:40]1[C:49]2[C:44](=[CH:45][C:46]([O:52][CH3:53])=[C:47]([O:50][CH3:51])[CH:48]=2)[N:43]=[CH:42][CH:41]=1)[NH2:35]>C(O)C.C1(C)C=CC=CC=1>[Cl:31][C:32]1[CH:33]=[C:34]([NH:35][C:26]([NH:25][C:23](=[O:24])[CH:22]([CH3:21])[CH2:28][CH2:29][CH3:30])=[S:27])[CH:36]=[CH:37][C:38]=1[O:39][C:40]1[C:49]2[C:44](=[CH:45][C:46]([O:52][CH3:53])=[C:47]([O:50][CH3:51])[CH:48]=2)[N:43]=[CH:42][CH:41]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 73412-Methylvaleric acidHCID 24386Thionyl ChlorideHCID 1073852-Methylvaleryl chlorideHCID 117390273-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]anilineHCID 218904792-Methylpentanoyl isothiocyanate

生成物 1

HCID 21891027N-{3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N'-(2-methylpentanoyl)thiourea
収率 94%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 1140Toluene溶媒2 回

反応条件

温度
100 °C

実験手順

Toluene (20 ml) and thionyl chloride (1 ml) were added to commercially available 2-methylpentanoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 2-methylpentanoyl isothiocyanate was prepared using the resultant 2-methylpentanoyl chloride as a starting compound according to the description of the literature. The resultant 2-methylpentanoyl isothiocyanate was dissolved in ethanol (1 ml) to prepare a solution. 3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline (50 mg), toluene (5 ml), and ethanol (1 ml) were added to the solution, and the mixture was stirred at room temperature for 16 hr. The reaction solution was concentrated, and the residue was purified by chromatography on silica gel using chloroform/acetone for development to give the title compound (69 mg, yield 94%).

後処理

  1. customThe solvent was removed by distillation, and 2-methylpentanoyl isothiocyanate
  2. customwas prepared
  3. customto prepare a solution
  4. concentrationThe reaction solution was concentrated
  5. customthe residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-e525d58f1bd44e74be3ea4546b6b9ba2
出典データセット
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07135466B2

反応ノート

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